


At Wit's End

by creepstiel



Category: Supernatural
Genre: Crying, Crying Dean, Daddy Kink, Dubious Consent, F/M, Female Dean, Forced Orgasm, High School Student Dean, Human Crowley, Multiple Orgasms, Overstimulation, Punishment, Spanking, Squirting, Teen Dean, Underage Dean, Vaginal Fingering, principal Crowley
Language: English
Status: Completed
Published: 2015-02-13
Updated: 2015-02-13
Packaged: 2018-03-12 03:56:39
Rating: Explicit
Warnings: Underage
Chapters: 1
Words: 1,479
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/3342767
Author URL: https://archiveofourown.org/users/creepstiel/pseuds/creepstiel
Summary: <blockquote class="userstuff">
              <p>Deanna is no stranger to the principal's office, she's one those <i>problem children</i>, with a dead mommy and a disdain for any kind of authority figure. And her <i>daddy issues</i>. She likes to cut class, smoke stolen cigarettes and/or inexpertly rolled joints behind the vocational building, get crass with everyone, and just be general rebellious pain in the faculty's ass. Mr. Crowley, however, is 1000% done with this bullshit and takes drastic measures. Deanna Winchester, after all, is a drastic girl.</p><p>So, while <i>this</i> may be new, it's clearly an unavoidable destiny.</p>
            </blockquote>





	At Wit's End

**Author's Note:**

> This porn exists thanks to this spnkinkmeme prompt:
> 
>  
> 
> Deanna gets sent to the principal for some sort of infraction. He gives her lashes, spanking her with a paddle or a ruler. Her short skirt exposes her panties when she's bent over and after spanking her the principal notices her white panties are so wet they're practically see through. He rubs her through her panties until she's panting and pushing back against him. Optional for him to slip his fingers into her panties and finger her and/or push her panties to the side and fuck her.
> 
> Principal can be anyone.

_Thwack._

_Thwack._

_Thwack._

In quick succession, Principal Crowley lands his weathered wooden ruler on Miss Winchester's very perky, very _naughty_ ass. He's actually lost count of how many smacks he has given the poor girl, probably thirty or so. That's a rough estimate.

You can't blame the man for getting distracted, especially with her flimsy excuse for a skirt, a short insubstantial (read: slutty) thing that had managed to ride up her thighs, exposing everything down there. Oh, the way that soft white cotton stretches tight over her bum. She won't stop squirming, biting her plump bottom lip raw. Fuck if that isn't a _sight_ to behold. And if he isn't mistaken, her eyes aren't the only thing getting wet.

"Now, now Deanna," he starts in a deceptively soothing tone, hushed but still rough at the edges because that's just his nature, isn't it? He rubs his palm across her lower back. "We're nearly finished. Just five more, you think you can count them out for me?"

"I- I maybe..." Her voice wavers off, her breath coming out shaky and deliciously uneven. Deanna is panting for him. "Yes."

Her bottom is smacked a few more times, hard. Crowley feels giddy just thinking about how red her ass must be.

"One, two, thre-eee." The last word is stuttered and broken by a keening whimper.

Her thighs are trembling, and Mr. Crowley would put his soul up for bet that her little cunt is altogether _throbbing_. She is so goddamn wet, he can smell it on her. She's positively dripping. He allows the ruler to slip out of his grasp, lets it hit the linoleum with a satisfying clang. He gives up the pretense of punishment now that he can see how much Deanna enjoys this. Her cute white panties are damn near translucent by now.

Her pussy lips are swollen, he can feel as much when his wicked fingers rub their way between her legs. She lets out a sexy little _unh_ noise and rocks back into his touch.

"Please."

It may be _dubious_ but it's all the consent he needs.

She reaches down, no doubt ready to rid herself of her sticky, dampened panties. He can see that she wants more than teasing over-the-fabric touches. Mr. Crowley is having none of that.

"Stop that," he grits out, pinching her inner thigh. He can't wait to see how ugly a bruise she gets; can't wait to suck on the tender, discolored flesh. Because this can't be a one time thing. "Right now. Hands on the desk. Fist 'em."

Deanna tenses but spreads her legs wider—an easy invitation. Her pussy and hands clench simultaneously. That's a neat trick. It earns, if not a reward, at least some positive reinforcement.

Mr. Crowley shoves his hand into her panties, 0% finesse and 100% sloppy eagerness in the face of things. They've got that in common.

He eases two fingers in, dragging them up and down her weeping inner walls. Deanna, though tight, isn't exactly _virgin_ tight. That makes it better. He thinks innocence and uncharted territory is far overrated.

"That feel good?"

"Ugh, yes." Deanna grunts.

"How many fingers do you think have been in your cunt?"

She is wiggling and trying to fuck herself on them, but he prevents it by moving with her. She pushes back, he pulls back.

"I don't know!" It comes out so fucking bratty, complete with a frustrated huff.

He only smirks, amused.

"Brat," he mumbles. He gives her another warning pinch, this time on her those sweet puffy lips. "Is that how you speak to Daddy?"

Deanna whimpers, her insides spasming around his fingers. It appears that he hit a nerve, a delicious nerve.

"'M sorry, _daddy._ "

He wasn't expecting her to actually enjoy that, to call him that. Daddy, of all things. If he were a man of weaker will, the inside of his pants would be a right creamy mess. As it stands, he has a damn impregnable will. It's strong enough for him to feign an air of casualness anyway.

"You bet your ass you're sorry."

"Yeah, well I bet something else." Deanna squeezes her legs closed, clenches her snatch in attempts to suck his fingers in deeper.

He really gives it to her then. He isn't going to quite call it fingerfucking, but it's a close enough imitation. It could fool some, but he knows he's on just the right side of gentle for it be honestly referred to as _fingering._ In, out, in, out, in, out. What can he say, he has a soft spot for little Miss Winchester. He wants to be a just a smidgeon of sweet with her. It proves enough to get her off though, and that's the important part.

Hell, if his office hadn't been soundproofed, he would be finding himself shortly unemployed—and in need of a lawyer—the noises and the volume on Deanna. As her first orgasm racks her body, her toes curl and she g r o a n s. She already starts to get the sleepy, dazed look too.

She has no idea.

"I'm not finished, sweetheart."

He plunges his fingers in deep, deeper. This is where she burns hottest. It's the place to _be_ if he wants his little princess thoroughly fucked. His thumb he fervently rubs over her clit, watching her eyes quickly well over with tears. If it wouldn't make for an awkward angle, Crowley would drape himself over the girl just to lick those salty drops from her flushed skin. It's a hell of a shame that he won't be tasting those today.

"What's, ah- ah- what is happening?" Her voice is higher pitched, breathless and panicked. A darling squeak falls from her mouth.

Oh, she is a _squirter_.

He laughs, not unkindly, at this discovery.

His wrist is getting soaked from how badly Deanna is gushing. He's guessing no one's ever made her squirt before or it just hasn't happened so _intensely_ because she seems confused. Embarrassed, even. She probably thinks she's just wet herself.

A sob bursts up, but he just keeps adding pressure. He doesn't stop rubbing there, rubbing her oversensitive nub, because she just keeps on keeping on. He drags the pads of his fingers across her folds, then on her abused little clitoris, over and over and over again—and she _comes_ over and over and over again.

"Daddy, daddy, daddy," she whimpers the D word repeatedly on a wet, drooling string. "Too- it's too much. Too good, I can't- I can't..  
Fuck."

"You _can._ "

And just to prove a point, Crowley forces one last orgasm out of her.

Her legs look ready to give out, so pushes her onto his desk with a put upon sigh. Ah, a principal's work is never done. He gives her a few minutes to get feeling back in all the places that ought to be feeling things. Then it's business as usual.

Well, business as will be usual soon. 

"Sorry, darling. This part isn't sexy at all, but it's necessary."

He hands her a handkerchief to wipe her sensitive bits off, turning his back on her to offer a sense of privacy. He knows _he_ wouldn't want anyone staring at him while he half-assedly cleans bodily fluids from his orifices. It only seems right to let her hang onto some of her dignity. It's that whole soft spot thing. 

"Thanks," she husks the word out, voice raw.

He can hear her sit up, a telling rustling of clothes. There is a quiet sniffling.

"I'm...uh-" a hiccup interrupts her. "I'm decent." 

He scoffs. 

"You're hardly decent, look at you." He _tsks_ but refrains from any other remarks, just fetches his overcoat from the rack. 

The smile she gives him when he lays that coat over her shoulders is sort of distracting. 

"Your skirt is ruined," he says, flippant. "And you're going to need something to cover yourself on the walk home. I'll ensure that you're excused from classes for the remainder of the day."

All she does is look at him expectantly, he sees out of the corner of his eye. 

This is it. 

"And... I'll be letting your, ah, father know that you're going to be having after school detention once a week for the foreseeable future." 

"Detention?" Deanna bats her eyelashes in his direction.

"Yes, you need firm discipline, you fucking slut brat." He's getting irritated, wants her to just leave already so he can jerk off and get on with his day. He does have _actual_ (legal) school-related things to do today, thank you very much

"Okay, daddy." She has to stand on tiptoes to kiss his cheek, "accidentally" brushing a hand over his crotch in the process. "See you later!"

With that, she runs out of his office, leaving him to mutter to himself and his dick. 

" _That bloody tease._ "

**Author's Note:**

> _f u c k I can't believe I even wrote this_


End file.
